Hydrochloric Acid → HCID 10806525, compound

HRID 1736235Notes

Reaction equation

HRID 1736235 reaction equation
[F:1][C:2]1[C:3]([OH:20])=[C:4]([C:10]([NH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([F:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[CH3:30][O:31][CH2:32]Cl.Cl>ClCCl>[F:1][C:2]1[C:3]([O:20][CH2:30][O:31][CH3:32])=[C:4]([C:10]([NH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([F:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 10803339HCID 10803339, compound

Product 1

HCID 10806525HCID 10806525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.72 g of the resulting ethyl 3,5-difluoro-6-(N-ethoxycarbonylamino)-2-hydroxybenzoate was dissolved in 70 ml of dichloromethane under argon atmosphere, 4.13 ml of diisopropylethylamine and 1.80 ml of chloromethyl methyl ether were added under ice-cooling and the mixture was stirred at 0 ° C. for 20 minutes. An aqueous dilute solution of hydrochloric acid was added to the reaction solution, the mixture was extracted with ether, the organic layer was washed with water and an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give ethyl 3,5-difluoro-6-(N-ethoxycarbonylamino)-2-methoxymethoxybenzoate.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ether
  3. washthe organic layer was washed with water
  4. dry with materialan aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-81500c756530452c8b04f09087204961
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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